Drape Yourself in Spooky Comfort at These October Events

We’ve waited all year and it’s finally here: the sensory explosion of October. Where temperatures are crisp, leaves turn gorgeous hues of orange and yellow (all the better to rail bike through), and the air is scented with—what is that? Ah, yes, PSL.

Lovers of all things spooky will especially rejoice (though, let’s face it, they’ve been celebrating Halloween since the beginning of September). But if you’re fright-averse, steel yourself: This is the season where benign abodes get a terrifying makeover, pumpkins are sparked ablaze for really no reason, and horror movie sets come to life. You may even see an elusive sasquatch or two.

So dig out those impossibly chunky sweaters and get ready for fall festivals, hayrides, new fuzzy friends, and gourds with names like “Warty Goblin.” And, as always—beware things that go bump in the night.

Fall is a time to get good and cozy, and what better way than to cuddle up to new soft buddies? 1,500 of them, to be exact, tromping through Sun Valley, Idaho in the Trailing of the Sheep Festival this month (Oct 5–9). There will be sheep tales, sheepdog trials, folk performances, historic wagons, and other stuff. But mainly, a whole lot of sheep. If you plan on going, the website asks that you leave your pups at home.

That same weekend is also Alpaca Fest Northwest, AKA Alpacapalooza, in Moses Lake, Washington, where you can meet similarly furry new pals who hopefully don’t spit on you (fun fact: you can even rent a room on an alpaca farm on Airbnb and Vrbo). Soonafter, the New York Sheep and Wool Festival (Oct 15–16) returns to Rhinebeck, with a Sunday morning llama parade and something called a Leaping Llama Contest—which you can bet we’ll be front and center to witness.

When the United States obtained the territory of Alaska from Russia for $7.2 million (less than 2 cents an acre, mind you), the formal ceremonial transfer of land took place on October 18, 1867. Dubbed Alaska Day, it’s now an annual state holiday, celebrated in the town of Sitka with three joyous days of parades, costume balls, gun salutes, sea kayak and other kinds of races, reenactments, and period costumes (think: beards and bonnets). Also pie.

But the day is not so celebratory for everyone—many in the Alaska Native community see their land as further stolen on that day, shuffled between two colonial entities. At the time, Native Alaskans laid claim to the territory, asserting that the US hadn’t actually bought the land, but the right to negotiate with them. They weren’t granted citizenship until 1924, and during the time in between, the US launched campaigns to eradicate their language and culture.

All of this to say, it’s a day for reflection. And whether you choose to check out the parade or explore an Indigenous museum in Anchorage, October is an excellent time to visit the 49th state. There’s plenty to do, from resplendent fall hikes to a chance to catch the northern lights before it gets too chilly, maybe even while dipping in Chena Hot Springs. For that, try the Aurora Winter Train, which runs on weekends.

Lumberjacks may have recently made a resurgence in the public mind—mostly because of that TikTok guy and his very, very thirsty followers (his name is Thoren for crying out loud)—but in Sheridan, Arkansas, the beginning of October has always been a good time to chop wood. The Timberfest Lumberjack Competition (Oct 7–8) pays tribute to the important state industry, and has been televised on ESPN with events like axe-throwing, horizontal chops, chainsaw competitions, and something called the Jack and Jill crosscut (Thoren, can you explain?). There’s also a parade, so throw on your best plaid Paul Bunyan duds and make a weekend of it.

Speaking of, while Fort Bragg, California’s Paul Bunyan Days has passed (mark your calendar for next year), the mythical superhuman still makes a massive impression as a roadside attraction, with quite a few statues of his likeness towering around the country. There’s a 31-foot tall one in Bangor, Maine, which claims to be the birthplace of Mr. Bunyan. Not to be outdone, so does Akeley, Minnesota, whose statue comes with a Paul Bunyan museum and their own festival. So, maybe they win. In fact, the state’s 10,000 lakes are said to be made by his gigantic footprints, and statuesque Bunyans are scattered all over the place (in addition to his lovely girlfriend Lucette, and his grave). Why not collect them all.

Did someone say pumpkins? This month, our favorite orange gourd comes to us in all forms. And they get competitive. Take the Safeway World Championship Pumpkin Weigh-Off in Half Moon Bay, California (Oct 10), where massive pumpkins go head-to-head for a chance at a $9-per-pound prize, plus an extra $30,000 mega-purse. (For reference, the current heavyweight champion pumpkin clocks in at 2,703 pounds.)

See giant gourds fashioned into boats at Tualatin, Oregon’s West Coast Giant Pumpkin Regatta (Oct 15–16), was them fly through the air at Punkin Chunkin in Clayton, NY (October 15) or Indiana’s Bloomington Pumpkin Launch (Oct 22), or catch them sporting elaborate paint jobs in Damariscotta, Maine, complete with their own regatta (Oct 7–9). And then, of course, spot them ablaze as professionally carved Jack-o-Lanterns everywhere from Rhode Island to Illinois to Upstate New York. Pumpkins! They’re not just for pie.

With all this talk of fall, we don’t want to lose sight of the fact that there’s still plenty of island time to be had. Like in the under-the-radar “Golden Isles,” of France, a gorgeous, car-free haven frequented by more sedate types than you’d find at the party locales of the French Riviera. Think a rugged, unspoiled national park, surrounded by powdery beaches, without a beach bar in sight.

But maybe you’re feeling the blue domes and whitewashed homes of Greece. We’ve got you covered there, with a list of the best beaches in the country. Even if you can’t go quite yet, it’s still a feast for the eyes.

And then there’s Mexico, and its all-inclusive resorts. Because sometimes you just want to not have to… think about anything. Lucky for you, the only thing you need to think about is which resort on this list you can see yourself checking into. But these aren’t your typical all-inclusives—they’re less all-you-can-eat and more rife with immersive cultural experiences. There are architecture tours and separate areas for families with kids and adults-only. There’s history and art and activities and… tequila. And if you want, none of those things. Spending all your time lazing on the beach works just as well.

Now on to another island, chillier but no less thrilling. Seafood fiends, take note: Prince Edward Island is open for business and making it very easy for you to sample their culinary bounty (donot leave without slurping some oysters). The Fall Flavours Festival runs through October 8, with events like the delightfully named Oysterlicious, a lobster party, deep sea fishing excursions, and harbor feasts promising hearty fare with tranquil views.

And while you have this charming island to yourself during shoulder season, you may as well get out and explore. Beyond shellfish, there’s red sand beaches and sandstone arches to complement dramatic leaf-peeping, an Anne of Green Gables museum, and plenty of hiking trails. Hit a haunted mansion then wind down by hopping breweries and distilleries. Seems like an ideal way to spend a fall weekend, if you ask us.

Did you know that there are currently thousands of miles of unused railroad track around the US, just hanging out like lazy metal snakes? Laid down during a time of expansion and industrial revolution, now they’re left to after-school shenanigans and indie horror films. But, not all of them. Some companies like Rail Explorers have restored the rails and turned them into playgrounds for open-air railbikes. So instead of being inside a train and enjoying the scenery and turning leaves from your window seat, you’re pedaling along while the wind whips through your hair. Maybe the leaves smack you in the face, but that’s all part of the fun.

Rail Explorers has five locations: Las Vegas, the Catskills, Cooperstown, Rhode Island, and their latest, Boone, Iowa. And that one’s a doozy, taking riders over the Bass Point Creek High Bridge suspended 156 feet above the ground. Just make sure you take everything out of your pockets before strapping in.

We’ve finally arrived at the best part of the month: Halloween. By the end of October, true enthusiasts have already been celebrating for two months straight—and scoped out all the best candy, of course. But if you still need spooky ideas, we’ve got you. Case in point? This busting-at-the seams list of the creepiest places in America.

We’re not just talking haunted houses here. No, those are too contrived for this list. We’re talking real live soul-tingling spots, like a playground built next to a cemetery in Alabama, and Arizona hotels stocked with ghosts that keep you up at night (sometimes they just want the company, ya know?). There’s a California canyon haunted by those who perished in a plane crash (California’s got their fair share of haunts, should you want to make it a road trip), cemeteries ridden with local lore, haunted state parks, creepy abandoned places, and former penitentiaries you can both tour and party in (see below). Plus much more. Including the very creepy Robert the Haunted Doll. He lives in Florida, naturally.

Even if you’ve never been inside the Eastern State Penitentiary in Philadelphia, if you’ve been anywhere in the area, you’ve definitely seen it. After all, it's hard to miss the massive Gothic Revival fortress’ hulking 30-foot walls. Opened in 1829, it served as an active prison until 1971, pioneering many of the incarceration policies still in place today (for better or for worse). Today, you can tour the space during the daylight hours (watch out for ghosts—it’s definitely haunted), hearing firsthand accounts from those who were locked up and perusing exhibits like Prisons Today, which dives into the current state of mass incarceration, or the Big Graph, which charts incarceration rates in the US by race and compares them to the rest of the world. Plus, an audio tour narrated by none other than Steve Buscemi.

To raise funds for its nonprofit work, ESP also throws what is probably one of the coolest Halloween events this side of the Atlantic.The party began as a candlelit tour and has blown up into a multi-night festival where visitors can wander the grounds popping into haunted houses (or, rather, cellblocks), seeing Al Capone’s cell (transformed into a speakeasy with flappers, of course), hang with a skeleton band, or explore a vampire crypt.

This year’s vendors include companies like Triple Bottom Brewing, which employs people who have experienced homelessness or incarceration. And Down North Pizza, which also hires the formerly incarcerated and has topped best restaurant lists from Bon Appetit to the New York Times (in addition to being recently named the best square slice in Philly).

Sometimes it’s not enough to just visit a creepy thing—you have to fully immerse yourself and dupe your brain into thinking it’s real. Enter the murder mystery party. Around since the 1930s, the precursor was apparently called Jury Box. Sold by Parker Brothers, it was a psychological twist on real life with players acting as members of a jury to determine the guilt or innocence of a fictitious character.

Today, you can purchase a party-in-a-box to create your own festivities (including that original Jury Box), or find some for free on the Internet. But for some real suspension of disbelief, don some period wear and attend one prepared by a professional. Our writer attended one in Oklahoma City (and was accused as the murderer… right away), but we’ve also got options in Michigan, Montana, New Hampshire, West Virginia, Kentucky, and California. That last one’s aboard the Napa Valley Wine Train. Because if anyone needs some booze to take the edge off, it’s an accused fake murderer.

Okay, you’ve got your famous spooky towns, your Salem, Massachusetts and your Sleepy Hollow, New York (pro-tip: if you visit Washington Irving’s grave at the Sleepy Hollow cemetery, make sure you know what time it closes. We learned the hard way).

But did you know there was also an actual Halloweentown? Located just 30 minutes outside of Portland in St. Helens, Oregon—where the Disney movie of the same name was filmed, no less—they throw a full month-and-a-half-long festival with haunted houses and hotels, and, of course, the lighting of a giant pumpkin. For something a little more sinister, visit iconic references from John Carpenter’s Halloween in his hometown of Bowling Green, Kentucky. Be sure to brush up on the movies beforehand—and keep your eyes peeled for masked asylum escapees wielding glinting butcher knives.

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